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Conformational Analysis, Molecular Structure and Solid State Simulation of the Antiviral Drug Acyclovir (Zovirax) Using Density Functional Theory Methods

Departamento de Química-Física I. Facultad de Ciencias Químicas, Universidad Complutense, Ciudad Universitaria, Madrid 28040, Spain
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Pharmaceuticals 2014, 7(6), 695-722; https://doi.org/10.3390/ph7060695
Received: 16 January 2014 / Revised: 22 May 2014 / Accepted: 26 May 2014 / Published: 6 June 2014
(This article belongs to the Special Issue Prodrugs: from Design to Clinic)
The five tautomers of the drug acyclovir (ACV) were determined and optimised at the MP2 and B3LYP quantum chemical levels of theory. The stability of the tautomers was correlated with different parameters. On the most stable tautomer N1 was carried out a comprehensive conformational analysis, and the whole conformational parameters (R, β, Φ, φ1, φ2, φ3, φ4, φ5) were studied as well as the NBO Natural atomic charges. The calculations were carried out with full relaxation of all geometrical parameters. The search located at least 78 stable structures within 8.5 kcal/mol electronic energy range of the global minimum, and classified in two groups according to the positive or negative value of the torsional angle j1. In the nitrogen atoms and in the O2' and O5' oxygen atoms of the most stable conformer appear a higher reactivity than in the natural nucleoside deoxyguanosine. The solid state was simulated through a dimer and tetramer forms and the structural parameters were compared with the X-ray crystal data available. Several general conclusions were emphasized. View Full-Text
Keywords: acyclovir; 9-(2-hydroxyethoxymethyl) guanine; tautomer; antiviral drug; conformational analysis; Zovirax acyclovir; 9-(2-hydroxyethoxymethyl) guanine; tautomer; antiviral drug; conformational analysis; Zovirax
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Alvarez-Ros, M.C.; Palafox, M.A. Conformational Analysis, Molecular Structure and Solid State Simulation of the Antiviral Drug Acyclovir (Zovirax) Using Density Functional Theory Methods. Pharmaceuticals 2014, 7, 695-722.

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